Methylamine → Ammonia

Participants

Reaction Steps

10% Palladium on carbon (0.2 g) was added to a solution of (2S,3R,4R,5R)-4-(benzoyloxy)-5-{2-cyano-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-2-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (1.0 g, 1.4 mmol) (Preparation 7) in 33% w/w methylamine in ethanol (75 ml). The reaction mixture was stirred under an atmosphere of hydrogen gas (4414 kPa, 60 psi) for 16 hours at room temperature. The solid was filtered off and the solvent was removed from the filtrate under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (90:10:1 by volume) to give the title compound (0.52 g) as a solid.

Provenance & Evidence